Dabco → 1-(1-Fluoromethyl-1-methyl-2-fluoroethyl)-6-fluoro-7-[(1S,6R)-2-oxa-5,8-diazabicyclo[4.3.0]non-8-yl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

HRID 367019Notes

Reaction equation

HRID 367019 reaction equation
[F:1][CH2:2][C:3]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:18])=[C:14](F)[CH:15]=2)[C:10](=[O:19])[C:9]([C:20]([OH:22])=[O:21])=[CH:8]1)([CH3:6])[CH2:4][F:5].[C@H:23]12[CH2:31][NH:30][CH2:29][C@H:28]1[NH:27][CH2:26][CH2:25][O:24]2.N12CCN(CC1)CC2>C(#N)C>[F:1][CH2:2][C:3]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:18])=[C:14]([N:30]3[CH2:31][C@H:23]4[C@H:28]([NH:27][CH2:26][CH2:25][O:24]4)[CH2:29]3)[CH:15]=2)[C:10](=[O:19])[C:9]([C:20]([OH:22])=[O:21])=[CH:8]1)([CH3:6])[CH2:4][F:5]

Participants

5

Reactant 3

HCID 9237DabcoHCID 18459849HCID 18459849, compoundHCID 55287490Rac-(4ar,7as)-octahydropyrrolo[3,4-b]morpholine

Product 1

HCID 540502771-(1-Fluoromethyl-1-methyl-2-fluoroethyl)-6-fluoro-7-[(1S,6R)-2-oxa-5,8-diazabicyclo[4.3.0]non-8-yl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(1-fluoromethyl-1-methyl-2-fluoroethyl)-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (400 mg, 1.26 mmol), (1S,6R)-2-oxa-5,8-diazabicyclo[4.3.0]nonane (176 mg, 1.39 mmol) and 1,4-diazabicyclo[2.2.2]octane (141 mg, 1.26 mmol) in absol. acetonitrile (20 ml) is heated under reflux overnight. After cooling the reaction mixture to room temperature, the precipitated crystals are filtered off and washed with acetonitrile.

Workup

  1. temperatureunder reflux overnight
  2. filtrationthe precipitated crystals are filtered off
  3. washwashed with acetonitrile

Sources & evidence

ORD record
ord-332ddb51c4364f45b52408de4a066de8
Source dataset
uspto-grants-2000_10
Patent number
US06133260

Reaction notes

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